Winthrop Vacations from $627

Book a Hotel + Flight or Car together to unlock savings

The Latest Winthrop vacation packages

Price found within the past 48 hours. Click for updated prices.

Super 8 by Wyndham Oelwein

$627

per person

Dec 20 - Dec 24

found 1 day ago

Roundtrip non-stop flight included

Richmond (RIC) to Waterloo (ALO)

8/10 Very Good! (180 reviews)

Cobblestone Inn & Suites – Manchester

$658

per person

Dec 20 - Dec 24

found 1 day ago

Roundtrip non-stop flight included

Richmond (RIC) to Waterloo (ALO)

9/10 Wonderful! (421 reviews)

Super 8 by Wyndham Waverly

$664

per person

Dec 20 - Dec 24

found 1 day ago

Roundtrip non-stop flight included

Richmond (RIC) to Waterloo (ALO)

8/10 Very Good! (484 reviews)

Super 8 by Wyndham Cedar Falls IA - University

$663

per person

Dec 20 - Dec 24

found 1 day ago

Roundtrip non-stop flight included

Richmond (RIC) to Waterloo (ALO)

8.4/10 Very Good! (1,001 reviews)

Isle Casino Hotel Waterloo - A Caesars Rewards Destination

$643

per person

Dec 20 - Dec 24

found 1 day ago

Roundtrip non-stop flight included

Richmond (RIC) to Waterloo (ALO)

8.4/10 Very Good! (1,007 reviews)

Great stay, beautiful room and a HUGE bathroom! Would be fantastic if there was a coffee maker in room. Or more choices in the coffee shop...and a person actually there to get you a cup of coffee. Waited for about 5 minutes or more, but no one showed up. Had to get to a funeral and had to go without our morning coffee. :(

Reviewed on Oct 25, 2026

Don't see what you're looking for?

See all available trips from Columbus to Winthrop

View all trips

Winthrop Hotel Deals

Urbana Inn & Suites

5369 Hutton Drive Urbana IA

$89 nightly

$93 total

Oct 26 - Oct 27

Total with taxes and fees

8.2/10 Very Good! (482 reviews)

"The pool was closed but no notice and not told at check in. We checked in at 3pm and it was closed…should tell your guests at check in when something is broken. Breakfast was pretty much nothing"

Reviewed on Oct 25, 2026

Cobblestone Inn & Suites – Manchester

1210 Commercial Court Manchester IA

Fully refundableReserve now, pay when you stay

$119 nightly

$134 total

Nov 2 - Nov 3

Total with taxes and fees

Cornerstone Inn & Suites

421 Rock Island Road Oelwein IA

Fully refundableReserve now, pay when you stay

$92 nightly

$103 total

Nov 24 - Nov 25

Total with taxes and fees

9.2/10 Wonderful! (549 reviews)

"Check in was fast, clean rooms, when there eas a problem with the sink, it was immediately taken care of."

Reviewed on Oct 21, 2026

See all 58 properties in Winthrop

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find the Best Winthrop Vacation Packages

Winthrop Essential Information

Language	English
Currency	U.S dollars
Population	850
Max Temp Winter	25ºF
Max Temp Summer	80ºF

More vacations you might like

Frequently asked questions

How much does a Winthrop vacation package cost?

You'll find cheap prices from $627 on Expedia for your Winthrop getaway. However, a range of factors like the hotel choice, length of stay and season will influence how much your vacation to Winthrop costs.

What are the cheapest months to go to Winthrop?

December, January and February are the best times to look for cheap Winthrop vacation packages. Traveling in quieter months means you can typically find lower prices on flights and accommodations.

How many days is enough for Winthrop?

Generally, a handful of days is enough to check out the major attractions during your Winthrop vacation. But if you'd like to have some time to rest or take day tours, consider extending your trip.

How to find the best Winthrop package deals?

Use Expedia's handy filters to help you find some fabulous Winthrop package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for Winthrop package deals in the low season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as early as possible.

Is it cheaper to book a Winthrop vacation as a package?

You can enjoy significant savings on your Winthrop break by booking a personalized vacation package. Click on the "Package" heading, then select your destination and travel dates to see some great hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.

When to book a vacation package to Winthrop?

If you're considering a spur-of-the-moment Winthrop adventure, check out our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can land amazing deals on your hotels and flights by booking ahead.

Does Expedia offer Book Now, Pay Later Winthrop vacation packages?

Set off on your perfect trip to Winthrop with help from Expedia's Book Now, Pay Later vacations. There's no need to save up or hold off until payday — we've partnered with online lender Affirm to give you financial flexibility. Our vacation packages with payment plans allow you to split the cost across 3, 6 or 12 months. With no hidden or late payment fees, it's easy to budget for your trip and snap up travel deals before they sell out.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.